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Klein is the former foreign editor of Newsweek and served as the editor-in-chief of The New York Times Magazine from 1977 to 1987. He frequently contributes to Vanity Fair and Parade and writes a weekly column in Parade called "Personality Parade" under the pseudonym "Walter Scott." (The Walter Scott pseudonym had originally been used by Lloyd Shearer, who wrote the column from 1958 to 1991.[1]) He also writes books, many of which have been on the New York Times Bestseller list. Additionally, he was the principal for the Business Communications School at The Euclid High School Complex. He was photographed by popular Humans of New York photographer Brandon Stanton, on June 12, 2014, which led to his personal website crashing due to a high volume of visitors.[2]

Klein is the father of two grown children, Karen (former manager of The Four Seasons restaurant in New York City), and Alec (a professor at Northwestern University).[3] He has been divorced twice. He was married to Dolores J. Barrett, senior vice president for Worldwide Public Relations at Polo Ralph Lauren, who died on 24 December 2013 in Manhattan.[4][5] Klein is the stepfather-in-law of Ruth Shalit.

Klein has been criticized for his biography of Hillary Clinton, titled, The Truth About Hillary: What She Knew, When She Knew It, and How Far She'll Go to Become President, which was released on June 21, 2005. Politico criticized the book for "serious factual errors, truncated and distorted quotes and overall themes [that] don't gibe with any other serious accounts of Clinton's life."[6] The book was attacked not only by liberals, but by conservatives as well. John Podhoretz wrote in the New York Post, "Thirty pages into it, I wanted to take a shower. Sixty pages into it, I wanted to be decontaminated. And 200 pages into it, I wanted someone to drive stakes through my eyes so I wouldn't have to suffer through another word."[7] In National ReviewJames Geraghty wrote, “Folks, there are plenty of arguments against Hillary Clinton, her policies, her views, her proposals, and her philosophies. This stuff ain’t it. Nobody on the right, left, or center ought to stoop to this level.”[8]